N′-[1-(4-Nitro­phen­yl)ethyl­idene]acetohydrazide

Li, Y.-F.; Du, L.-C.; Jian, F.-F.

doi:10.1107/S1600536808040919

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o74

doi:10.1107/S1600536808040919

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N′-[1-(4-Nitrophenyl)ethylidene]acetohydrazide

Yu-Feng Li,^a Lian-Cai Du ^b and Fang-Fang Jian ^c ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, ^bMicroscale Science Institute, Bioengineering Institute, Weifang University, Weifang 261061, People's Republic of China, and ^cMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 28 October 2008; accepted 4 December 2008; online 10 December 2008)

The title compound, C₁₀H₁₁N₃O₃, was prepared by the reaction of acetohydrazide and 1-(4-nitrophenyl)ethanone. The asymmetric unit contains two crystallographically independent molecules. Inversion-related molecules form dimers, in which two N—H⋯O hydrogen bonds generate an intermolecular R₂²(8) ring.

Related literature

For possibile analytical applications of Schiff bases, see: Cimerman et al. (1997 ). For a related structure, see: Girgis (2006 ).

Experimental

Crystal data

C₁₀H₁₁N₃O₃
M_r = 221.22
Triclinic, $[P \overline 1]$
a = 8.4453 (17) Å
b = 9.5438 (19) Å
c = 14.820 (3) Å
α = 72.66 (3)°
β = 77.37 (3)°
γ = 75.59 (3)°
V = 1090.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6035 measured reflections
4037 independent reflections
2570 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.159
S = 1.04
4037 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.84 (3)	2.16 (3)	2.989 (3)	170 (2)
N4—H4A⋯O4ⁱⁱ	0.88 (3)	2.08 (3)	2.952 (3)	172 (2)
C4—H4B⋯N1	0.96	2.42	2.826 (3)	105
C4—H4B⋯O1ⁱ	0.96	2.28	3.243 (3)	175
C10—H10A⋯O6ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C14—H14A⋯N4	0.96	2.41	2.821 (3)	105
C14—H14A⋯O4ⁱⁱ	0.96	2.36	3.317 (3)	173
C16—H16A⋯O3^iv	0.93	2.50	3.388 (4)	159
C20—H20A⋯N5	0.93	2.43	2.740 (3)	100
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z+1; (iii) x, y+1, z; (iv) x-1, y, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040919/at2663sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040919/at2663Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman, et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.

As shown in Fig. 1, the asymmetric unit contains two crystallographically independent molecules. The C3—N2 bond length of 1.277 (3) Å and C13—N5 bond length of 1.287 (3) Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006).

In the structure, there exist C-H···O, C-H···N and N-H···N hydrogen bonding interactions. Inversion-related molecules form a dimer structure, in which two N—H···O hydrogen bonds generate an intermolecular R₂²(8) ring (Table 1).

Related literature top

For possibile analytical applications of Schiff bases, see: Cimerman et al. (1997). For a related structure, see: Girgis (2006).

Experimental top

A mixture of the acetohydrazide (0.1 mol), and 1-(4-nitrophenyl)ethanone (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.086 mol, yield 86%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-[1-(4-Nitrophenyl)ethylidene]acetohydrazide top

Crystal data top

C₁₀H₁₁N₃O₃	Z = 4
M_r = 221.22	F(000) = 464
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4453 (17) Å	Cell parameters from 1553 reflections
b = 9.5438 (19) Å	θ = 2.9–23.0°
c = 14.820 (3) Å	µ = 0.10 mm⁻¹
α = 72.66 (3)°	T = 293 K
β = 77.37 (3)°	Block, yellow
γ = 75.59 (3)°	0.25 × 0.20 × 0.18 mm
V = 1090.7 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2570 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 25.5°, θ_min = 2.3°
ϕ and ω scans	h = −10→10
6035 measured reflections	k = −8→11
4037 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0784P)² + 0.1468P] where P = (F_o² + 2F_c²)/3
4037 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₀H₁₁N₃O₃	γ = 75.59 (3)°
M_r = 221.22	V = 1090.7 (4) Å³
Triclinic, P1	Z = 4
a = 8.4453 (17) Å	Mo Kα radiation
b = 9.5438 (19) Å	µ = 0.10 mm⁻¹
c = 14.820 (3) Å	T = 293 K
α = 72.66 (3)°	0.25 × 0.20 × 0.18 mm
β = 77.37 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2570 reflections with I > 2σ(I)
6035 measured reflections	R_int = 0.027
4037 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.159	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
4037 reflections	Δρ_min = −0.21 e Å⁻³
297 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N5	0.6357 (2)	0.18317 (19)	0.43057 (12)	0.0478 (4)
N4	0.6040 (2)	0.3087 (2)	0.46328 (13)	0.0517 (5)
C20	0.7190 (3)	−0.0804 (3)	0.37732 (16)	0.0553 (6)
H20A	0.7913	−0.0577	0.4076	0.066*
O4	0.6882 (2)	0.4455 (2)	0.53613 (14)	0.0762 (6)
C13	0.5290 (2)	0.1642 (2)	0.38741 (14)	0.0463 (5)
C15	0.5727 (3)	0.0223 (2)	0.35793 (14)	0.0458 (5)
C18	0.6510 (3)	−0.2475 (3)	0.30826 (16)	0.0540 (6)
C19	0.7587 (3)	−0.2144 (3)	0.35260 (17)	0.0585 (6)
H19A	0.8567	−0.2814	0.3657	0.070*
C16	0.4685 (3)	−0.0151 (3)	0.31179 (16)	0.0574 (6)
H16A	0.3708	0.0516	0.2975	0.069*
N6	0.6913 (3)	−0.3924 (2)	0.28399 (15)	0.0688 (6)
C12	0.7182 (3)	0.3345 (3)	0.50456 (18)	0.0597 (6)
O6	0.5902 (3)	−0.4215 (2)	0.24812 (16)	0.0985 (7)
O5	0.8220 (3)	−0.4769 (2)	0.30177 (14)	0.0845 (6)
C14	0.3713 (3)	0.2712 (3)	0.36615 (19)	0.0659 (7)
H14A	0.3614	0.3568	0.3898	0.099*
H14B	0.2794	0.2229	0.3967	0.099*
H14C	0.3719	0.3028	0.2982	0.099*
C17	0.5074 (3)	−0.1501 (3)	0.28661 (17)	0.0629 (6)
H17A	0.4370	−0.1738	0.2556	0.076*
N2	0.3467 (2)	0.3952 (2)	0.09154 (13)	0.0517 (5)
O1	−0.0396 (2)	0.6256 (2)	0.07168 (13)	0.0729 (5)
N1	0.1929 (2)	0.4531 (2)	0.06573 (15)	0.0559 (5)
C10	0.6576 (3)	0.3176 (2)	0.14039 (15)	0.0505 (5)
H10A	0.5893	0.4061	0.1507	0.061*
C3	0.4436 (3)	0.2916 (2)	0.05675 (15)	0.0497 (5)
C8	0.9053 (3)	0.1382 (3)	0.15882 (16)	0.0537 (6)
C5	0.6075 (3)	0.2378 (2)	0.09008 (15)	0.0468 (5)
C6	0.7135 (3)	0.1075 (3)	0.07434 (17)	0.0601 (6)
H6A	0.6834	0.0534	0.0402	0.072*
C9	0.8052 (3)	0.2683 (2)	0.17494 (16)	0.0532 (6)
H9A	0.8369	0.3222	0.2087	0.064*
C7	0.8626 (3)	0.0568 (3)	0.10851 (18)	0.0640 (7)
H7A	0.9327	−0.0307	0.0977	0.077*
C2	0.0951 (3)	0.5678 (3)	0.09904 (17)	0.0555 (6)
N3	1.0610 (3)	0.0837 (3)	0.19712 (18)	0.0759 (6)
C1	0.1551 (3)	0.6207 (3)	0.16819 (19)	0.0722 (7)
H1B	0.0741	0.7025	0.1856	0.108*
H1C	0.2574	0.6534	0.1390	0.108*
H1D	0.1724	0.5402	0.2244	0.108*
C4	0.4032 (3)	0.2229 (3)	−0.0121 (2)	0.0814 (9)
H4B	0.2938	0.2695	−0.0264	0.122*
H4C	0.4084	0.1176	0.0160	0.122*
H4D	0.4816	0.2376	−0.0701	0.122*
O3	1.0875 (3)	0.1457 (3)	0.2518 (2)	0.1159 (9)
O2	1.1593 (3)	−0.0208 (3)	0.1728 (2)	0.1231 (10)
C11	0.8785 (3)	0.2256 (3)	0.5105 (3)	0.0922 (10)
H11A	0.9474	0.2574	0.5410	0.138*
H11B	0.9331	0.2208	0.4471	0.138*
H11C	0.8582	0.1285	0.5470	0.138*
H4A	0.513 (3)	0.378 (3)	0.4600 (17)	0.071 (8)*
H1A	0.162 (3)	0.426 (3)	0.0248 (17)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N5	0.0487 (10)	0.0441 (10)	0.0552 (10)	−0.0028 (8)	−0.0128 (8)	−0.0215 (8)
N4	0.0477 (11)	0.0475 (11)	0.0665 (12)	0.0030 (9)	−0.0180 (9)	−0.0281 (9)
C20	0.0533 (13)	0.0543 (14)	0.0685 (15)	−0.0050 (11)	−0.0214 (11)	−0.0269 (12)
O4	0.0687 (11)	0.0712 (12)	0.1096 (14)	0.0064 (9)	−0.0348 (10)	−0.0562 (11)
C13	0.0445 (11)	0.0492 (13)	0.0455 (11)	−0.0056 (10)	−0.0105 (9)	−0.0132 (10)
C15	0.0492 (12)	0.0451 (12)	0.0441 (11)	−0.0079 (10)	−0.0100 (9)	−0.0122 (9)
C18	0.0669 (15)	0.0476 (13)	0.0536 (13)	−0.0128 (11)	−0.0091 (11)	−0.0209 (10)
C19	0.0583 (14)	0.0495 (14)	0.0731 (15)	−0.0017 (11)	−0.0171 (12)	−0.0262 (12)
C16	0.0570 (13)	0.0577 (14)	0.0645 (14)	−0.0059 (11)	−0.0239 (11)	−0.0204 (12)
N6	0.0906 (17)	0.0570 (14)	0.0680 (13)	−0.0219 (13)	−0.0070 (12)	−0.0275 (11)
C12	0.0513 (13)	0.0621 (15)	0.0749 (16)	0.0020 (11)	−0.0226 (12)	−0.0328 (13)
O6	0.1239 (17)	0.0867 (15)	0.1170 (17)	−0.0298 (13)	−0.0324 (14)	−0.0567 (13)
O5	0.0999 (16)	0.0583 (12)	0.0976 (15)	−0.0030 (11)	−0.0112 (12)	−0.0367 (11)
C14	0.0587 (15)	0.0656 (16)	0.0808 (17)	0.0078 (12)	−0.0275 (13)	−0.0345 (13)
C17	0.0732 (16)	0.0644 (16)	0.0653 (15)	−0.0189 (13)	−0.0224 (13)	−0.0250 (13)
N2	0.0469 (10)	0.0518 (11)	0.0593 (11)	−0.0039 (9)	−0.0174 (9)	−0.0169 (9)
O1	0.0565 (10)	0.0775 (12)	0.0890 (12)	0.0072 (9)	−0.0307 (9)	−0.0306 (10)
N1	0.0523 (11)	0.0576 (12)	0.0642 (12)	−0.0025 (9)	−0.0227 (10)	−0.0222 (10)
C10	0.0500 (13)	0.0439 (12)	0.0622 (13)	−0.0045 (10)	−0.0143 (10)	−0.0204 (10)
C3	0.0524 (13)	0.0453 (13)	0.0557 (13)	−0.0062 (10)	−0.0169 (10)	−0.0164 (10)
C8	0.0481 (12)	0.0546 (14)	0.0582 (13)	−0.0047 (11)	−0.0146 (10)	−0.0141 (11)
C5	0.0485 (12)	0.0460 (12)	0.0483 (12)	−0.0071 (10)	−0.0115 (9)	−0.0148 (10)
C6	0.0635 (15)	0.0550 (14)	0.0718 (15)	0.0016 (12)	−0.0231 (12)	−0.0330 (12)
C9	0.0518 (13)	0.0522 (14)	0.0634 (14)	−0.0092 (11)	−0.0140 (11)	−0.0237 (11)
C7	0.0594 (15)	0.0549 (15)	0.0794 (17)	0.0070 (12)	−0.0170 (12)	−0.0305 (13)
C2	0.0506 (13)	0.0542 (14)	0.0624 (14)	−0.0043 (11)	−0.0173 (11)	−0.0148 (11)
N3	0.0552 (13)	0.0743 (16)	0.1008 (18)	0.0038 (12)	−0.0305 (12)	−0.0271 (13)
C1	0.0635 (15)	0.0743 (18)	0.0880 (19)	0.0043 (13)	−0.0270 (14)	−0.0383 (15)
C4	0.0746 (18)	0.087 (2)	0.105 (2)	0.0091 (15)	−0.0418 (16)	−0.0579 (18)
O3	0.0844 (15)	0.132 (2)	0.159 (2)	0.0139 (14)	−0.0718 (15)	−0.0699 (18)
O2	0.0765 (14)	0.1116 (19)	0.196 (3)	0.0364 (14)	−0.0630 (16)	−0.0769 (19)
C11	0.0635 (17)	0.089 (2)	0.148 (3)	0.0211 (15)	−0.0522 (18)	−0.070 (2)

Geometric parameters (Å, º) top

N5—C13	1.287 (3)	N1—C2	1.349 (3)
N5—N4	1.368 (2)	N1—H1A	0.83 (2)
N4—C12	1.353 (3)	C10—C9	1.372 (3)
N4—H4A	0.88 (3)	C10—C5	1.397 (3)
C20—C19	1.376 (3)	C10—H10A	0.9300
C20—C15	1.398 (3)	C3—C5	1.489 (3)
C20—H20A	0.9300	C3—C4	1.500 (3)
O4—C12	1.231 (3)	C8—C9	1.371 (3)
C13—C15	1.481 (3)	C8—C7	1.376 (3)
C13—C14	1.493 (3)	C8—N3	1.460 (3)
C15—C16	1.391 (3)	C5—C6	1.389 (3)
C18—C17	1.367 (3)	C6—C7	1.380 (3)
C18—C19	1.374 (3)	C6—H6A	0.9300
C18—N6	1.472 (3)	C9—H9A	0.9300
C19—H19A	0.9300	C7—H7A	0.9300
C16—C17	1.389 (3)	C2—C1	1.492 (3)
C16—H16A	0.9300	N3—O2	1.218 (3)
N6—O6	1.222 (3)	N3—O3	1.219 (3)
N6—O5	1.223 (3)	C1—H1B	0.9600
C12—C11	1.489 (3)	C1—H1C	0.9600
C14—H14A	0.9600	C1—H1D	0.9600
C14—H14B	0.9600	C4—H4B	0.9600
C14—H14C	0.9600	C4—H4C	0.9600
C17—H17A	0.9300	C4—H4D	0.9600
N2—C3	1.277 (3)	C11—H11A	0.9600
N2—N1	1.368 (3)	C11—H11B	0.9600
O1—C2	1.232 (3)	C11—H11C	0.9600

C13—N5—N4	119.06 (18)	C5—C10—H10A	119.3
C12—N4—N5	119.98 (19)	N2—C3—C5	115.09 (19)
C12—N4—H4A	114.2 (17)	N2—C3—C4	125.2 (2)
N5—N4—H4A	125.8 (17)	C5—C3—C4	119.7 (2)
C19—C20—C15	121.5 (2)	C9—C8—C7	122.0 (2)
C19—C20—H20A	119.2	C9—C8—N3	118.9 (2)
C15—C20—H20A	119.2	C7—C8—N3	119.1 (2)
N5—C13—C15	114.65 (18)	C6—C5—C10	117.9 (2)
N5—C13—C14	125.5 (2)	C6—C5—C3	122.1 (2)
C15—C13—C14	119.81 (19)	C10—C5—C3	120.00 (19)
C16—C15—C20	117.6 (2)	C7—C6—C5	121.2 (2)
C16—C15—C13	121.3 (2)	C7—C6—H6A	119.4
C20—C15—C13	121.07 (18)	C5—C6—H6A	119.4
C17—C18—C19	121.9 (2)	C8—C9—C10	118.8 (2)
C17—C18—N6	119.2 (2)	C8—C9—H9A	120.6
C19—C18—N6	118.9 (2)	C10—C9—H9A	120.6
C18—C19—C20	118.9 (2)	C8—C7—C6	118.7 (2)
C18—C19—H19A	120.6	C8—C7—H7A	120.7
C20—C19—H19A	120.6	C6—C7—H7A	120.7
C17—C16—C15	121.3 (2)	O1—C2—N1	119.6 (2)
C17—C16—H16A	119.4	O1—C2—C1	122.2 (2)
C15—C16—H16A	119.4	N1—C2—C1	118.3 (2)
O6—N6—O5	123.9 (2)	O2—N3—O3	122.8 (2)
O6—N6—C18	117.5 (2)	O2—N3—C8	118.8 (2)
O5—N6—C18	118.5 (2)	O3—N3—C8	118.4 (2)
O4—C12—N4	120.0 (2)	C2—C1—H1B	109.5
O4—C12—C11	121.8 (2)	C2—C1—H1C	109.5
N4—C12—C11	118.2 (2)	H1B—C1—H1C	109.5
C13—C14—H14A	109.5	C2—C1—H1D	109.5
C13—C14—H14B	109.5	H1B—C1—H1D	109.5
H14A—C14—H14B	109.5	H1C—C1—H1D	109.5
C13—C14—H14C	109.5	C3—C4—H4B	109.5
H14A—C14—H14C	109.5	C3—C4—H4C	109.5
H14B—C14—H14C	109.5	H4B—C4—H4C	109.5
C18—C17—C16	118.8 (2)	C3—C4—H4D	109.5
C18—C17—H17A	120.6	H4B—C4—H4D	109.5
C16—C17—H17A	120.6	H4C—C4—H4D	109.5
C3—N2—N1	120.00 (19)	C12—C11—H11A	109.5
C2—N1—N2	119.4 (2)	C12—C11—H11B	109.5
C2—N1—H1A	118.7 (16)	H11A—C11—H11B	109.5
N2—N1—H1A	121.5 (16)	C12—C11—H11C	109.5
C9—C10—C5	121.4 (2)	H11A—C11—H11C	109.5
C9—C10—H10A	119.3	H11B—C11—H11C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.84 (3)	2.16 (3)	2.989 (3)	170 (2)
N4—H4A···O4ⁱⁱ	0.88 (3)	2.08 (3)	2.952 (3)	172 (2)
C4—H4B···N1	0.96	2.42	2.826 (3)	105
C4—H4B···O1ⁱ	0.96	2.28	3.243 (3)	175
C10—H10A···O6ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C14—H14A···N4	0.96	2.41	2.821 (3)	105
C14—H14A···O4ⁱⁱ	0.96	2.36	3.317 (3)	173
C16—H16A···O3^iv	0.93	2.50	3.388 (4)	159
C20—H20A···N5	0.93	2.43	2.740 (3)	100

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁N₃O₃
M_r	221.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4453 (17), 9.5438 (19), 14.820 (3)
α, β, γ (°)	72.66 (3), 77.37 (3), 75.59 (3)
V (Å³)	1090.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6035, 4037, 2570
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.159, 1.04
No. of reflections	4037
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.84 (3)	2.16 (3)	2.989 (3)	170 (2)
N4—H4A···O4ⁱⁱ	0.88 (3)	2.08 (3)	2.952 (3)	172 (2)
C4—H4B···N1	0.96	2.42	2.826 (3)	105
C4—H4B···O1ⁱ	0.96	2.28	3.243 (3)	175
C10—H10A···O6ⁱⁱⁱ	0.93	2.49	3.216 (3)	135
C14—H14A···N4	0.96	2.41	2.821 (3)	105
C14—H14A···O4ⁱⁱ	0.96	2.36	3.317 (3)	173
C16—H16A···O3^iv	0.93	2.50	3.388 (4)	159
C20—H20A···N5	0.93	2.43	2.740 (3)	100

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x−1, y, z.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Girgis, A. S. (2006). J. Chem. Res. pp. 81–85. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Page o74

doi:10.1107/S1600536808040919

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